Have I got a loose ?

I am a young adult, I have had a fair amount of in the past. However, I have always been referred as having a tight p*ssy with my ex boyfriend and it seemed that way to me too. But now I have a new boyfriend and we've had .. and sometimes when he is inside me it isn't even arousing because it is just as though he hasn't entered me. I can always feel him inside me, but it feels as though I am loose because my doesn't wrap around his . He once was inside me.. and he shockingly asked me "am I in??" It annoyed me, because that's something he should have known from the feeling and another time I was on top of him and he asked me if I could squeeze my l muscles tight.. and I didn't know how to do that and I felt upset and embarred. At first I thought it was because we don't normally use a condom as contraception so we both get very lubricated with both bodily fluids with takes away the tightness. But then I noticed even using a condom it is the same, I lately mastered to squeeze my muscles and it feels better, it isn't very tight, but the feeling is a lot better for me, and I think he has noticed too and he seems to enjoy it more. But I still hate this feeling that I have to squeeze my just for good .